Galectin-inhibitory thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells

J Med Chem. 2008 Dec 25;51(24):8109-14. doi: 10.1021/jm801077j.


Aromatic 3,3'-diesters of thiodigalactoside were synthesized in a rapid three-step sequence from commercially available thiodigalactoside and evaluated as inhibitors of cancer- and immunity-related galectins. For each of galectins-1, -3, -7, and -9N-terminal domain, aromatic 3,3'-diesters of thiodigalactoside were found to have affinities in the low micromolar range, which represents a 7-70 fold enhancement over thiodigalactoside itself. No significant improvement was found for galectin-8 N-terminal domain. Two of the compounds were selected for testing in cell culture and were shown to have potent antimigratory effects on human PC-3 prostate and human A549 nonsmall-cell lung cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Movement
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Esters
  • Galectins / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Kinetics
  • Lung Neoplasms / therapy*
  • Male
  • Models, Chemical
  • Prostatic Neoplasms / therapy*
  • Protein Structure, Tertiary
  • Thiogalactosides / chemistry
  • Thiogalactosides / metabolism*


  • Esters
  • Galectins
  • Thiogalactosides
  • thiodigalactoside